Journal of the American Chemical Society

Conformationally restricted TRH analogs: the compatibility of a 6, 5-bicyclic lactam-based mimetic with binding to TRH-R

W Li, KD Moeller

Index: Li, Wenhao; Moeller, Kevin D. Journal of the American Chemical Society, 1996 , vol. 118, # 42 p. 10106 - 10112

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Citation Number: 59

Abstract

A pair of conformationally restricted TRH analogs have been synthesized. Both analogs have the central histidine of TRH replaced by a cyclohexylalanine unit, and both analogs contain a 6, 5-bicyclic lactam ring fusing the proline peptide bond into a trans conformation. The analogs differ at the bridgehead stereocenter. The synthesis of the analogs utilized an anodic amide oxidation reaction to selectively functionalize a proline derivative and a ...